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607-80-7,MFCD00216134
Catalog No.:AA0037CH

607-80-7 | Sesamin

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25mg
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50mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0037CH
Chemical Name:
Sesamin
CAS Number:
607-80-7
Molecular Formula:
C20H19O6
Molecular Weight:
355.3613
MDL Number:
MFCD00216134
SMILES:
C1OC2=CC=[CH](C=C2O1)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc2c(c1)OCO2
Properties
Properties
 
BP:
504.4°C at 760 mmHg  
Form:
Solid  
MP:
121-123°C  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
482  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
6  
Rotatable Bond Count:
2  
XLogP3:
2.7  

Literature

Title: Discovery of a sesamin-metabolizing microorganism and a new enzyme.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20160809

Title: Sesamin ameliorates doxorubicin-induced cardiotoxicity: involvement of Sirt1 and Mn-SOD pathway.

Journal: Toxicology letters 20140113

Title: Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages.

Journal: Journal of ethnopharmacology 20130307

Title: Sesamin protects mouse liver against nickel-induced oxidative DNA damage and apoptosis by the PI3K-Akt pathway.

Journal: Journal of agricultural and food chemistry 20130206

Title: Comparison of metabolism of sesamin and episesamin by drug-metabolizing enzymes in human liver.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20121001

Title: Sesamin modulates gene expression without corresponding effects on fatty acids in Atlantic salmon (Salmo salar L.).

Journal: Lipids 20120901

Title: (+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.

Journal: Bioorganic & medicinal chemistry letters 20120815

Title: Chondroprotective and anti-inflammatory effects of sesamin.

Journal: Phytochemistry 20120801

Title: Modulatory effects of sesamin on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells.

Journal: Neuropharmacology 20120601

Title: Tolbutamide hydroxylation by hepatic microsomes from Atlantic salmon (Salmo salar L.).

Journal: Molecular biology reports 20120601

Title: Quercetin and sesamin protect neuronal PC12 cells from high-glucose-induced oxidation, nitrosative stress, and apoptosis.

Journal: Rejuvenation research 20120601

Title: Plasma and tissue concentrations of α-tocopherol and δ-tocopherol following high dose dietary supplementation in mice.

Journal: Nutrients 20120601

Title: Sesamin exerts renoprotective effects by enhancing NO bioactivity in renovascular hypertensive rats fed with high-fat-sucrose diet.

Journal: European journal of pharmacology 20120515

Title: Anti-inflammatory and PPAR transactivational effects of secondary metabolites from the roots of Asarum sieboldii.

Journal: Bioorganic & medicinal chemistry letters 20120401

Title: How is sesamin metabolised in the human liver to show its biological effects?

Journal: Expert opinion on drug metabolism & toxicology 20120101

Title: Comparative effects of sesame seed lignan and flaxseed lignan in reducing the growth of human breast tumors (MCF-7) at high levels of circulating estrogen in athymic mice.

Journal: Nutrition and cancer 20120101

Title: [Anti-lipotoxic action of sesamin on renovascular hypertensive rats fed with a high-fat, high-sucrose diet].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20120101

Title: Sesamin stimulates osteoblast differentiation through p38 and ERK1/2 MAPK signaling pathways.

Journal: BMC complementary and alternative medicine 20120101

Title: Identification of the metabolites of episesamin in rat bile and human liver microsomes.

Journal: Biological & pharmaceutical bulletin 20120101

Title: Quercetin and sesamin protect dopaminergic cells from MPP+-induced neuroinflammation in a microglial (N9)-neuronal (PC12) coculture system.

Journal: Oxidative medicine and cellular longevity 20120101

Title: A phytochemical investigation of Zanthoxylum setulosum.

Journal: Natural product communications 20111201

Title: Sesamin induces melanogenesis by microphthalmia-associated transcription factor and tyrosinase up-regulation via cAMP signaling pathway.

Journal: Acta biochimica et biophysica Sinica 20111001

Title: Experimental antithrombotic effects of sesame seed whole grains and extracts.

Journal: Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20110901

Title: Sequential metabolism of sesamin by cytochrome P450 and UDP-glucuronosyltransferase in human liver.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110901

Title: Sesamin induces autophagy in colon cancer cells by reducing tyrosine phosphorylation of EphA1 and EphB2.

Journal: International journal of oncology 20110701

Title: Sesamin inhibits macrophage-induced vascular endothelial growth factor and matrix metalloproteinase-9 expression and proangiogenic activity in breast cancer cells.

Journal: Inflammation 20110601

Title: Involvement of heme oxygenase-1 induction via Nrf2/ARE activation in protection against H2O2-induced PC12 cell death by a metabolite of sesamin contained in sesame seeds.

Journal: Bioorganic & medicinal chemistry 20110315

Title: Genotoxicity evaluation of sesamin and episesamin.

Journal: Mutation research 20110203

Title: Influence of dietary sesamin, a bioactive compound on fatty acids and expression of some lipid regulating genes in Baltic Atlantic salmon (Salmo salar L.) juveniles.

Journal: Physiological research 20110101

Title: The mechanism underlying the synergetic hypocholesterolemic effect of sesamin and α-tocopherol in rats fed a high-cholesterol diet.

Journal: Journal of pharmacological sciences 20110101

Title: Sesamin ameliorates oxidative stress and mortality in kainic acid-induced status epilepticus by inhibition of MAPK and COX-2 activation.

Journal: Journal of neuroinflammation 20110101

Title: Fatty acids and gene expression responses to bioactive compounds in Atlantic salmon (Salmo salar L.) hepatocytes.

Journal: Neuro endocrinology letters 20110101

Title: Absolute configuration of antifibrotic (+)-episesamin isolated from Lindera obtusiloba BLUME.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20110101

Title: Metabolism of sesamin by cytochrome P450 in human liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20101201

Title: Obtusilactone A and (-)-sesamin induce apoptosis in human lung cancer cells by inhibiting mitochondrial Lon protease and activating DNA damage checkpoints.

Journal: Cancer science 20101201

Title: A new 3,4-seco-lupane-type triterpenoid from the pulp of Acanthopanax senticosus (Rupr. et Maxim) Harms.

Journal: Natural product research 20101001

Title: Sesamin attenuates intercellular cell adhesion molecule-1 expression in vitro in TNF-alpha-treated human aortic endothelial cells and in vivo in apolipoprotein-E-deficient mice.

Journal: Molecular nutrition & food research 20100901

Title: Antioxidants from the leaves of Cinnamomum kotoense.

Journal: Natural product communications 20100601

Title: Sesamin manifests chemopreventive effects through the suppression of NF-kappa B-regulated cell survival, proliferation, invasion, and angiogenic gene products.

Journal: Molecular cancer research : MCR 20100501

Title: Sesquiterpenes from Oplopanax horridus.

Journal: Journal of natural products 20100423

Title: Specific dietary polyphenols attenuate atherosclerosis in apolipoprotein E-knockout mice by alleviating inflammation and endothelial dysfunction.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20100401

Title: Sesamin attenuates behavioral, biochemical and histological alterations induced by reversible middle cerebral artery occlusion in the rats.

Journal: Chemico-biological interactions 20100105

Title: Angiogenic activity of sesamin through the activation of multiple signal pathways.

Journal: Biochemical and biophysical research communications 20100101

Title: Assessing the neuroprotective effect of antioxidant food factors by application of lipid-derived dopamine modification adducts.

Journal: Methods in molecular biology (Clifton, N.J.) 20100101

Title: Effects of dietary ingredients on function and expression of P-glycoprotein in human intestinal epithelial cells.

Journal: Biological & pharmaceutical bulletin 20100101

Title: Sesamin mitigates inflammation and oxidative stress in endothelial cells exposed to oxidized low-density lipoprotein.

Journal: Journal of agricultural and food chemistry 20091209

Title: Use of high resolution LC-MSn analysis in conjunction with mechanism-based stress studies: identification of asarinin, an impurity from sesame oil in an animal health product.

Journal: Journal of pharmaceutical and biomedical analysis 20091205

Title: Metabolic engineering of lignan biosynthesis in Forsythia cell culture.

Journal: Plant & cell physiology 20091201

Title: Antirejection effect of Herba Asari extract in rats after cardiac allograft implantation.

Journal: Transplantation proceedings 20091201

Title: Inhibition of 20-hydroxyeicosatetraenoic acid synthesis using specific plant lignans: in vitro and human studies.

Journal: Hypertension (Dallas, Tex. : 1979) 20091101

Title: Sesamin improves endothelial dysfunction in renovascular hypertensive rats fed with a high-fat, high-sucrose diet.

Journal: European journal of pharmacology 20091012

Title: Effects of a diet rich in sesame ( Sesamum indicum) pericarp on the expression of oestrogen receptor alpha and oestrogen receptor beta in rat prostate and uterus.

Journal: The British journal of nutrition 20090901

Title: Sesamin as a co-initiator for unfilled dental restorations.

Journal: Acta biomaterialia 20090901

Title: [Studies on the chemical constituents from Euphorbia chrysocoma].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20090901

Title: Metabolites of sesamin, a major lignan in sesame seeds, induce neuronal differentiation in PC12 cells through activation of ERK1/2 signaling pathway.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20090701

Title: Effect of schisandrin B and sesamin mixture on CCl(4)-induced hepatic oxidative stress in rats.

Journal: Phytotherapy research : PTR 20090201

Title: Antihypertensive effects of sesamin in humans.

Journal: Journal of nutritional science and vitaminology 20090201

Title: Amides and benzenoids from Zanthoxylum ailanthoides with inhibitory activity on superoxide generation and elastase release by neutrophils.

Journal: Journal of natural products 20090101

Title: Assessing the neuroprotective effect of antioxidative food factors by application of lipid-derived dopamine modification adducts.

Journal: Methods in molecular biology (Clifton, N.J.) 20090101

Title: Effect of the form of the sesame-based diet on the absorption of lignans.

Journal: The British journal of nutrition 20081201

Title: Sesamin supplementation increases white muscle docosahexaenoic acid (DHA) levels in rainbow trout (Oncorhynchus mykiss) fed high alpha-linolenic acid (ALA) containing vegetable oil: metabolic actions.

Journal: Lipids 20081101

Title: Sesamin increases alpha-linolenic acid conversion to docosahexaenoic acid in atlantic salmon (Salmo salar L.) hepatocytes: role of altered gene expression.

Journal: Lipids 20081101

Title: First chemical synthesis of antioxidative metabolites of sesamin.

Journal: Chemical & pharmaceutical bulletin 20081101

Title: HPTLC fingerprinting and quantification of lignans as markers in sesame oil and its polyherbal formulations.

Journal: Journal of pharmaceutical and biomedical analysis 20080805

Title: Dietary tocotrienol reduces UVB-induced skin damage and sesamin enhances tocotrienol effects in hairless mice.

Journal: Journal of nutritional science and vitaminology 20080401

Title: Dietary sesamin suppresses aortic NADPH oxidase in DOCA salt hypertensive rats.

Journal: Clinical and experimental pharmacology & physiology 20080301

Title: Constituents of Asarum sieboldii with inhibitory activity on lipopolysaccharide (LPS)-induced NO production in BV-2 microglial cells.

Journal: Chemistry & biodiversity 20080201

Title: A survey of sesamin and composition of tocopherol variability from seeds of eleven diverse sesame (Sesamum indicum L.) genotypes using HPLC-PAD-ECD.

Journal: Phytochemical analysis : PCA 20080101

Title: Sesamin modulates tyrosine hydroxylase, superoxide dismutase, catalase, inducible NO synthase and interleukin-6 expression in dopaminergic cells under MPP+-induced oxidative stress.

Journal: Oxidative medicine and cellular longevity 20080101

Title: Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida.

Journal: Journal of natural products 20071001

Title: Sesamin, a lignan of sesame, down-regulates cyclin D1 protein expression in human tumor cells.

Journal: Cancer science 20070901

Title: Anti-inflammatory benzenoids from Antrodia camphorata.

Journal: Journal of natural products 20070601

Title: Suppression of ochratoxin biosynthesis by naturally occurring alkaloids.

Journal: Food additives and contaminants 20070401

Title: Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats.

Journal: The British journal of nutrition 20070101

Title: An efficient and stereoselective dearylation of asarinin and sesamin tetrahydrofurofuran lignans to acuminatolide by methyltrioxorhenium/H(2)O(2) and UHP systems.

Journal: Journal of natural products 20070101

Title: Electrospray ionization ion-trap time-of-flight tandem mass spectrometry of two furofurans: sesamin and gmelinol.

Journal: Rapid communications in mass spectrometry : RCM 20070101

Title: Effect of sesamin on serum cholesterol and triglycerides levels in LDL receptor-deficient mice.

Journal: European journal of nutrition 20061201

Title: Sesamin metabolites induce an endothelial nitric oxide-dependent vasorelaxation through their antioxidative property-independent mechanisms: possible involvement of the metabolites in the antihypertensive effect of sesamin.

Journal: The Journal of pharmacology and experimental therapeutics 20060701

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Decomposition reaction of sesamin in supercritical water.

Journal: Bioscience, biotechnology, and biochemistry 20060501

Title: Dietary sesamin and docosahexaenoic and eicosapentaenoic acids synergistically increase the gene expression of enzymes involved in hepatic peroxisomal fatty acid oxidation in rats.

Journal: Metabolism: clinical and experimental 20060301

Title: Antioxidant activity and bioactive compounds of tea seed (Camellia oleifera Abel.) oil.

Journal: Journal of agricultural and food chemistry 20060208

Title: The epimerization of sesamin and asarinin.

Journal: Journal of natural products 20051101

Title: Sesamin ingestion regulates the transcription levels of hepatic metabolizing enzymes for alcohol and lipids in rats.

Journal: Alcoholism, clinical and experimental research 20051101

Title: NMR spectroscopic, mass spectroscopic, X-ray crystallographic, and theoretical studies of molecular mechanics of natural products: farformolide B and sesamin.

Journal: Biophysical chemistry 20050401

Title: Sesamin inhibits lipopolysaccharide-induced cytokine production by suppression of p38 mitogen-activated protein kinase and nuclear factor-kappaB.

Journal: Immunology letters 20050215

Title: Antioxidative catechol lignans converted from sesamin and sesaminol triglucoside by culturing with Aspergillus.

Journal: Journal of agricultural and food chemistry 20050112

Title: Effect of sesamin in Acanthopanax senticosus HARMS on behavioral dysfunction in rotenone-induced parkinsonian rats.

Journal: Biological & pharmaceutical bulletin 20050101

Title: Modulating effect of sesamin, a functional lignan in sesame seeds, on the transcription levels of lipid- and alcohol-metabolizing enzymes in rat liver: a DNA microarray study.

Journal: Bioscience, biotechnology, and biochemistry 20050101

Title: Sesamin induces nitric oxide and decreases endothelin-1 production in HUVECs: possible implications for its antihypertensive effect.

Journal: Journal of hypertension 20041201

Title: Effects of vitamin E and sesamin on hypertension and cerebral thrombogenesis in stroke-prone spontaneously hypertensive rats.

Journal: Clinical and experimental pharmacology & physiology 20041201

Title: Consumption of sesame oil muffins decreases the urinary excretion of gamma-tocopherol metabolites in humans.

Journal: Annals of the New York Academy of Sciences 20041201

Title: Dietary sesame oils inhibits iron-induced oxidative stress in rats [corrected].

Journal: The British journal of nutrition 20041001

Title: Lignoids in insects: chemical probes for the study of ecdysis, excretion and Trypanosoma cruzi-triatomine interactions.

Journal: Toxicon : official journal of the International Society on Toxinology 20040915

Title: Protective effects of sesamin and sesamolin on murine BV-2 microglia cell line under hypoxia.

Journal: Neuroscience letters 20040826

Title: Antifungal constituents of Melicope borbonica.

Journal: Phytotherapy research : PTR 20040701

Title: Interaction of dietary fat types and sesamin on hepatic fatty acid oxidation in rats.

Journal: Biochimica et biophysica acta 20040601

Title: Insecticidal activity of chemical constituents from Aristolochia pubescens against Anticarsia gemmatalis larvae.

Journal: Pest management science 20040401

Title: Species differences in the physiological activity of dietary lignan (sesamin and episesamin) in affecting hepatic fatty acid metabolism.

Journal: The British journal of nutrition 20040301

Title: Free radical scavenging behavior of antioxidant compounds of sesame (sesamum indicum L.) in DPPH(*) system.

Journal: Journal of agricultural and food chemistry 20040225

Title: Antioxidative roles of sesamin, a functional lignan in sesame seed, and it's effect on lipid- and alcohol-metabolism in the liver: a DNA microarray study.

Journal: BioFactors (Oxford, England) 20040101

Title: Effects of sesamin on aortic oxidative stress and endothelial dysfunction in deoxycorticosterone acetate-salt hypertensive rats.

Journal: Biological & pharmaceutical bulletin 20031201

Title: Effects of sesamin and capsaicin on the mRNA expressions of delta6 and delta5 desaturases in rat primary cultured hepatocytes.

Journal: Journal of nutritional science and vitaminology 20031201

Title: Protective effect of sesamin administration on exercise-induced lipid peroxidation.

Journal: International journal of sports medicine 20031001

Title: Protective effects of sesamin and sesamolin on hypoxic neuronal and PC12 cells.

Journal: Journal of neuroscience research 20031001

Title: Effect of dietary fat level and sesamin on the polyunsaturated fatty acid metabolism in rats.

Journal: Journal of nutritional science and vitaminology 20031001

Title: Dietary sesame lignans decrease lipid peroxidation in rats fed docosahexaenoic acid.

Journal: Journal of nutritional science and vitaminology 20030801

Title: Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides.

Journal: Planta medica 20030401

Title: Novel antioxidative metabolites in rat liver with ingested sesamin.

Journal: Journal of agricultural and food chemistry 20030312

Title: Antioxidant and anti-inflammatory effects of a diet supplemented with sesamin on hepatic ischemia-reperfusion injury in rats.

Journal: Hepato-gastroenterology 20030101

Title: Combined effects of dietary conjugated linoleic acid and sesamin triacylglycerol and ketone body production in rat liver.

Journal: Journal of nutritional science and vitaminology 20021001

Title: Antihypertensive effect of sesamin. IV. Inhibition of vascular superoxide production by sesamin.

Journal: Biological & pharmaceutical bulletin 20020901

Title: Determination of L-sesamin and L-asarinin in Zanthoxylum(Roxb.) DC. by high performance liquid chromatography.

Journal: Di 1 jun yi da xue xue bao = Academic journal of the first medical college of PLA 20020701

Title: Short and stereoselective total synthesis of furano lignans (+/-)-dihydrosesamin, (+/-)-lariciresinol dimethyl ether, (+/-)-acuminatin methyl ether, (+/-)-sanshodiol methyl ether, (+/-)-lariciresinol, (+/-)-acuminatin, and (+/-)-lariciresinol monomethyl ether and furofuran lignans (+/-)-sesamin, (+/-)-eudesmin, (+/-)-piperitol methyl ether, (+/-)-pinoresinol, (+/-)-piperitol, and (+/-)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source.

Journal: The Journal of organic chemistry 20020517

Title: Sesamin, a sesame lignan, decreases fatty acid synthesis in rat liver accompanying the down-regulation of sterol regulatory element binding protein-1.

Journal: Biochimica et biophysica acta 20011130

Title: Effects of vitamin E and sesamin on hypertension and cerebral thrombogenesis in stroke-prone spontaneously hypertensive rats.

Journal: Hypertension research : official journal of the Japanese Society of Hypertension 20011101

Title: Dietary manipulations of body fat-reducing potential of conjugated linoleic acid in rats.

Journal: Bioscience, biotechnology, and biochemistry 20011101

Title: C-H insertion approach to the synthesis of endo,exo-furofuranones: synthesis of (+/-)-asarinin, (+/-)-epimagnolin A, and (+/-)-fargesin.

Journal: The Journal of organic chemistry 20011005

Title: Effect of sesame seeds rich in sesamin and sesamolin on fatty acid oxidation in rat liver.

Journal: Journal of agricultural and food chemistry 20010501

Title: Effect of sesamin on mitochondrial and peroxisomal beta-oxidation of arachidonic and eicosapentaenoic acids in rat liver.

Journal: Lipids 20010501

Title: [Studies on the chemical constituents of the herba of Cuscuta chinensis].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20010501

Title: Sesamin a potent antifeedant principle from Piper mullesua.

Journal: Phytotherapy research : PTR 20010201

Title: Effects of dietary sesame seeds on plasma tocopherol levels.

Journal: Nutrition and cancer 20010101

Title: Separation and NMR studies on lignans of Raulinoa echinata.

Journal: Phytochemical analysis : PCA 20010101

Title: Differential in vitro anti-HIV activity of natural lignans.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 19900101

Title: Cheng FC, et al. Neuroprotective effects of sesamin and sesamolin on gerbil brain in cerebral ischemia. Int J Biomed Sci. 2006 Sep;2(3):284-8.

Title: Shimizu S, et al. Sesamin is a potent and specific inhibitor of delta 5 desaturase in polyunsaturated fatty acidbiosynthesis. Lipids. 1991 Jul;26(7):512-6.

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